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Unlocking the Potential of CF3-Alkynes in Gold-Catalyzed Oxygen Transfer: A Direct Route to Trifluoromethylated
Polina F Kotikova1, Dmitry V Dar'in1, Vadim Yu Kukushkin1,2
1Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation.
Abstract:
We report on gold-catalyzed oxygen transfer utilizing, for the first time, electron-deficient trifluoromethylated alkynes as substrates. This double O-transfer process provides a direct and convenient one-step route to difficult-to-obtain trifluoromethylated 1,2-diketones. Due to the relatively mild oxidative reaction conditions (rt to 60 °C, 2,6-dichloropyridine N-oxide as an oxidizer, 3 mol % JohnPhosAuNTf2), various functional substituents were tolerated (19 examples; yields up to 95%). The synthetic utility of the obtained trifluoromethylated dicarbonyl products was further explored, and these studies included one-pot multicomponent syntheses of valuable CF3-substituted indoles and benzofurans.
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